


Getting his Buddy Laid

by eackermann0



Category: Original Work
Genre: Anal Sex, Cisgender, F/M, Multi, Threesome - F/F/M, Transgender
Language: English
Status: Completed
Published: 2021-01-27
Updated: 2021-01-27
Packaged: 2021-03-13 11:54:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,864
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29028294
Author URL: https://archiveofourown.org/users/eackermann0/pseuds/eackermann0
Summary: James and Aaron had been best friend's since they were four years old. Aaron was currently dating James' sister, which he felt bad about. To make up for it he's trying to get James laid, but it's not going well. Turns out James isn't much of a man. Aaron has an idea though: what if James wasn't a man at all.
Kudos: 1





	Getting his Buddy Laid

James and Aaron had been best friends since they were only four years old. As  
the two grew older, they didn't grow apart, but they did grow up in very  
different ways. James was an effeminate nerd while Aaron had turned into an  
absolute stud. He could fuck any woman he wanted and right now that woman was  
James' twin sister, Jade. The twins weren't technically identical, but you  
wouldn't know that from looking at them. They had the same long brown hair,  
emerald green eyes, thin body, and bubble butt.

Aaron wasn't exactly proud of fucking his friend's sister, though he enjoyed her  
thoroughly. He knew it made James uncomfortable and wanted to make it up to him  
the best way he could: by getting James laid. Unfortunately, that hasn't gone so  
well so far.

*DING DONG*

"Hi Aaron," said James.

"Hey buddy. How'd things go with Rebecca? Did you seal the deal?"

James looked down.

"Oh, uh. No, she... she broke up with me."

"Aww, that sucks. It's okay though, there's always next time."

"Let's go up to my room and-"

"Sorry buddy, no can do. I actually came to fuck Jade," Aaron said as he walked  
in the door and up the stairs to Jade's room, "but I'll come hang out with you  
when you're done."

James waited a few minutes until he heard the sounds of his sister being railed  
by his best friend, then went up to his room. The room next door to his  
sister's. He was ashamed of it, but James loved to jerk off to the sound of his  
friend fucking Jade.

"FUCK, FUCK, FUCK. Fuck me Aaron, fuck me with your big dick."

"You like this big dick?"

"I love it. I love your dick!"

James came several times to the sounds coming from his sister's room. When Aaron  
was done with James sister, he left her room and entered James'.

"Have fun buddy?"

"What do you mean?"

"You don't have to hide it. I know you jerk off to us."

"N-no I don't."

"First of all, that was the least convincing denial I've ever heard. Second, you  
could have stayed downstairs, but instead you decided to sit in here, where I no  
you can hear your sister screaming. Third, every time I come in here after I  
fuck Jade it smells like cum."

James stayed silent and Aaron gave him a look that said: "I'm waiting."

"Okay, yeah I jerk off when you guys... y'know."

"That's okay. I'm glad you get something out of it. You know I've always felt  
bad about banging your sister."

"I know. And I appreciate how hard you've tried to get me laid, but I just don't  
think it's going to happen."

"Don't say that. Of course it's going to happen, you just need the right girl."

"You've set me up with seven different girls."

"Well help me out here. You always seem to do fine at first. Hell girls love you  
cause you're cute."

"I... I don't want to talk about it."

"If you can be honest about jerking off to be fucking your sister, I think you  
can tell me this."

"I have a small dick."

"Oh... I... Well I don't know what we can do about that... Is it that small."

"It's two inches."

"Well, so you're a grower not a shower-"

"Two inches hard. You can barely see it when it's soft."

"Oh... sorry man."

"It's okay. You've been a great friend. You tried so hard to find me a girl..."

"Don't give up yet... I'll think of something."

"I appreciate that, but I really don't think there's anything you can do."

\--------------------

Aaron left that day racking his brain trying to find someway James could  
overcome his literal shortcoming. Unfortunately, he had nothing. The next day  
her returned to James and Jade's house to once again plow Jade. The two lay  
together in their afterglow.

"What are you thinking about over there?" asked Jade.

"Your brother."

"Uh, what?"

"Not like that! You know how I keep trying to set him up with girls?"

"Yeah."

"And you know how it never works out?"

"Yeah."

"Well, it turns out it's because he's got a small dick."

"It can't be *that* small."

"He said it's two inches hard."

"Damn. I don't think I'd even feel that."

"Yeah, I'm sure all those girls thought the same thing."

"So what now?"

"I don't know."

"Damn, with a dick that small he may as well cut it off and become a girl. We  
could really be twins then."

Aaron's eyes lit up.

"That's it!"

"What?"

"Maybe instead of trying to get him laid with girls, he can *be* the girl."

"Dude, that was just a joke."

"I know, but think about it. You two are basically identical. Put a bra on him  
and you'd look the same."

"Yeah, he is kind of girly."

"And he's got a nice butt too."

"And apparently you want to fuck my brother's ass."

"I kind of do now... I wanted to fuck yours too, but you wouldn't let me."

"And you think James is going to go for this?"

"I don't know... maybe. It's not like he has many other options."

Aaron got up and he went over to James' room.

"You guys were quiet for a while," said James.

"We were just talking. Actually, we were talking about you."

"About me?"

"Yeah. Jade gave me a pretty good idea of how to solve our problem."

"Our problem?"

"Y'know, getting you laid?"

"Right. So what's this new plan of yours."

"Okay, this is going to sound crazy..."

"Ooookayyyy..."

"What if, instead of getting you with a girl, we turn you into the girl."

James just stared at Aaron like he hadn't even spoken English.

"Well?" asked Aaron.

"You're right, that is crazy."

"I know, but hear me out."

"I'm listening..."

James sighed trying to think of the words.

"Okay... I'm sorry if this comes off as harsh, but here it is. Let's be honest,  
you're barely a man as it is. You have a tiny dick, a cute girly face, you're  
thin like a girl, and you've got a big butt like a girl."

James laid back in his chair, defeated.

"So that's it? I just give up and become a girl?"

"I think you'd be happier as a successful girl than a failed man."

"Are you going to come by tomorrow?"

"I can."

"Please? I'll think about it until then."

"Okay... thanks for hearing me out."

\--------------------

Aaron returned to the Jame's house for the third day in a row, this time to see  
James and not his sister. The two boys sat in James room.

"So let's say I want to become a girl, what does that look like."

"Well there's hormone treatments and stuff you can go on. They can do surgery  
too. They can give you a pussy if you want one."

"That seems a little..."

"Okay, okay. As far as right now, your sister said if you decide you want to be  
a girl, she'd help you out. She can help you dress like a girl and do makeup and  
stuff."

"Won't a look ridiculous?"

"Not at all. You look just like your sister. I bet you'll be one of the cutest  
girls around."

"You really think that? You're not just messing with me?"

"I mean it. I promise you, I mean it."

"Sooo when I become a girl... are you going to..."

"What?"

"Are you going to fuck me?"

"I'd like to. But that's up to you."

"Well I mean... obviously it's going to be you right? Who else would I have fuck  
me?"

"In that case, yes, I'd gladly fuck you."

"I've heard you and sis... I've heard the stuff sis says about... about your  
dick. Is it big?"

"Yeah, it's not a bad size."

"C-can I see it."

Aaron smiled, unzipped his pants, and released his throbbing member.

"Holy shit. You're hung like a pornstar."

"Sorry, I like to under sell it a little. It makes the girl's reactions better.  
Like yours."

"I don't know if that's going to fit in me."

"It will. Not right now, but if you play with yourself you should be able to  
stretch enough to fit me inside you. Pornstars do it all the time."

"Yeah, but I'm not a pornstar."

"Seriously, we'll get you some buttplugs and dildos of different sizes and  
you can work your way up to taking my big dick."

"Okay..."

James couldn't help but stare at Aaron's massive cock.

"You can come get a closer look if you want."

James got up and went over to his friend where he dropped to his knees to admire  
this dick in front of him.

"Do you want to feel it?"

James reached a hand out tentatively and wrapped it around Aaron's cock. He  
started jerking him.

"That's good. That's good, Jamie."

"J-Jamie?"

"You're a girl now right? Girls aren't named James, they're named Jamie."

"Okay."

"You're doing good. Keep jerking me. Use your mouth too."

"I- I don't know..."

"It's okay. Just start by licking the head."

Jamie leaned down and gave the head of Aaron's cock a lick. Then another. Then  
another.

"Do you like the taste of my precum?"

"A little..."

"I'm glad you do. Think you can suck on it now?"

Jamie stopped licking and put the head in his mouth. Inside he continued licking  
the head while he bobbed up and down as much as he could.

"That's perfect Jamie. Yeah, you'll definitely make a good girl. My good girl."

"Th-thanks."

"Just keep sucking. I'm almost there Jamie."

Jamie did as she was told. She even tried to go the extra mile, she let some of  
her saliva drip down onto his shaft and used it to jerk him off better.

"I'm going to cum. Swallow it for me. Will you do that Jamie? Will you swallow  
my cum?"

Jamie nodded her head while still sucking him. Moments later he was blasting a  
massive load into her mouth. She did her best to swallow it, but some managed to  
dribble down her chin.

"Unh, good girl. Now go clean up for me."

Jame went to the bathroom and cleaned herself up then came back to her room. She  
went to go sit in her chair, but was pulled down into Aaron's lap. The two  
looked into each other's eyes.

"Did you like that?" asked Aaron.

"Yes."

"You liked sucking my big dick?"

"I liked sucking your big dick."

"And swallowing my cum?"

"And I liked swallowing your cum."

Aaron leaned in and kissed Jamie and Jamie kissed him back.

"Are you my girl now?"

"Yes, I'm your girl now. You've got both sisters."

"You know just what to say to me."

\--------------------

Jamie received some clothes from Jade that she would fit in. He was still  
keeping his transition a secret from his mother, but at least around Aaron he  
was able to dress like a girl. Aaron ordered Jamie a collection of buttplugs  
and dildos of increasing sizes so she could stretch or asshole wide enough  
for him to use. Jamie started off too scared to even use the toys, but  
eventually he did and slowly but surely he worked his way up to the largest  
size, which Aaron measured to be roughly the same as his own size. When Jamie  
finally had the largest dildo up her ass she had to call Aaron and let him know. 

"Hello?"

"Aaron?"

"What's up Jamie?"

"I did it. I can take the largest dildo."

"You did it? You had the whole thing in you?"

"I'm sitting on it right now."

"Is your mom home?"

"Nope. She's working late and won't be home until tonight."

"Don't move from that spot. I'll be there in ten minutes."

Aaron made the trip in eight. He entered Jamie's room to find her still sitting  
on the massive purple dildo he had bought her. He dropped his pants and released  
his equally large authentic cock. He then presented it to Jamie to suck. Jamie,  
determined to be Aaron's good girl, went right to work on him bobbing up and  
down taking as much as she could. She received some tips from her sister and had  
been blowing Aaron over the past few weeks while she couldn't yet take him in  
her back passage. She still couldn't swallow the whole thing, but she could  
manage a few inches in her throat.

"That's enough, I just need you to get me hard. Where's your lube?"

Jamie grabbed the lube off her desk and handed it to Aaron. Aaron quickly lubed  
himself up before grabbing Jamie and lifting her off her dildo, leaving her  
feeling empty. Aaron carried him over to the bed, where he sat both of them  
down, impaling Jamie on with his cock instantly.

"Aaron it's in... Your dick is in me!"

"It sure is. Now be a good girl and work that ass on my dick."

Jamie did as she was told, lifting her ass up and bringing it back down, taking  
his cock to the hilt each time.

"Does my good girl like my dick?"

"Yes, unh, I love your dick."

"Better than the dildo?"

"Yes. Nothing can compare to the real thing. It's so warm and... it's attached  
to you."

Aaron brought his hands up and groped his friend's jiggling ass cheeks. 

"I feel the same way about this big ass of yours. I'd have never told you this  
before, cause I didn't want to sound gay, but you used to drive me crazy when  
your wore tight shorts."

"All my shorts were tight. Either they fit my ass and were way to big on my  
waist, or they fit my waist and were tight around my ass."

Jamie laid back, getting tired from her previous position, and started doing  
circles with her ass in Aaron's crotch.

"I used to hate my fat ass... I think I've learned to love it now though."

"I think you'll have an easier time finding shorts now, since you'll be  
shopping in the women's section."

Jamie resumed her previous motion, bouncing on her best friend's dick.

"Unnh, Jamie I'm almost there."

"Cum in me."

"You want my cum in your ass?"

"Yes. Fill your good girl up."

Aaron sat up and grabbed Jamie's ass bouncing it up and down on his cock faster  
than Jamie was able to do my herself. At the same time he leaned in and kissed  
his best friend.

"I love you, Jamie."

"I love you too."

Aaron exploded in Jamie's ass fucking his cum into her. When he was finally  
spent he leaned back onto the bed. Jamie rolled over and laid on her side facing  
Aaron. Cum flowed out of her ass and onto the bed.

At this point Jade chose to reveal herself, she had watch the entire scene  
through a crack in the door.

"Just to be clear," asked Jade, "I'm not being replaced right?"

"I've got enough love for both of you," replied Aaron, "If that's okay with  
you."

"I don't mind sharing," said Jamie.

"So you're greedy, huh? You want *both* sisters?" asked Jade.

"I think I already have both sisters."

"Greedy and cocky? You almost make me want to say no."

"But then you'd be robbed of this big dick you love so much," said Jamie,  
flopping his dick around to make his point.

"You've got me there."

Jade came in and tried to ride Aaron's re-hardening member, but he stopped her.

"Wait, I have to go clean up first. You're not supposed to go from ass to  
pussy. You could get an infection or something."

"Oh fine."

Aaron got up and went to clean himself.

"Move over sis."

Jamie laid on her stomach in her bed the normal way. Jade laid down next to  
her on her back.

"It's been a crazy few weeks hasn't it?"

"Yeah. I'd have thought you were crazy if you told me a month ago I'd be a girl  
and getting fucked by Aaron."

"My brother became a sister and now she's fucking my boyfriend."

"He was arguably mine first."

"You brought him around, but I sealed the deal."

"You're not bad though... right?"

"No sis, I'm not mad. He's been your friend forever and I know you guys have a  
special relationship. Plus I'm hoping the temptation of your ass will keep him  
away from mine."

The sisters laughed together. Aaron soon returned to the room.

"Damn, that's a nice sight," said Aaron, admiring the sisters.

"Don't keep me waiting any longer," said Jade.

Aaron got on the bed over Jade and entered her.

"Fuck I needed this. I got so wet watching you fuck my sister."

Meanwhile Aaron noticed Jamie laying next to them with her ass sticking out like  
a beautiful moon. He couldn't resist reaching over and having a feel of Jamie's  
ass cheek.

"Hey!" shouted Jade, "Don't feel my sister up while you're fucking me!"

"I couldn't help it. She's just got that big ass out like that. I still haven't  
fucked her from behind."

"Still? We've only done it once," said Jamie.

"Yeah, but I've wanted to for years."

"I bet this'll get your attention," said Jade. She leaned over and kissed Jamie  
on the lips. First just a peck, then a proper french kiss. The two sisters  
kissed and explored each other's bodies. Aaron looked on in awe as he fucked  
Jade. Jamie reached down and found her sister's clit. She rubbed it as her best  
friend fucked Jade's pussy.

"Oh fuck... Jamie... Keep doing that... I-I'm cumming."

Jade was brought to orgasm and Aaron wasn't far behind, blowing his load in  
Jade's pussy. Aaron leaned back and sat at the other end of the bed, between the  
two girls' legs. They all just laid there for a while, until finally Jamie broke  
the silence.

"Hey Aaron?"

"Yeah Jamie?"

"Think you've got another one in you?" she asked as she propped her ass up with  
her legs and spread her cheeks.

"For you? I think I can do one more."

Aaron got up and positioned himself behind his friend ready to fuck her doggy  
style.

"Do you think you're still lubed up?" asked Aaron.

"I'm pretty sure I've still got about a gallon of your cum in me... If you don't  
mind your own sloppy seconds that is."

Jamie got her answer in the form of her friend's now cum covered cock being  
buried deep in her ass. Aaron groped Jamie's ass as he fucked it.

"I love how big and soft your ass is. It's like I bounce off of it every time I  
put it in you."

"I love the way you fill me up."

"Fuck back against me."

Jamie started bouncing her ass back against Aaron as he fucked her.

"Like this?"

"Perfect. That's my good girl."

"You're never that gentle and sweet with me," said Jade.

"You act like I treat you bad."

"I didn't say that. It's just, you've always been protective of James, and now  
you're so loving to Jamie. I wouldn't mind being treated that way sometimes."

"Okay, I hear you. I'll try to be soft with you too."

"I mean... I think you've called me bitch more than you've called me your good  
girl."

"Is somebody jealous? Does Jade want to be my good girl too?"

"...yes."

"So why are you like that with me? I mean, you've always been nice to me, even  
when I was a dude, but this is different."

"I just wanted to make you feel like a girl. So I thought the best way to do  
that was to be sweet and loving. If you don't like it-"

"No! I like it.... I love it. I'm your good girl."

Aaron laughed at her.

"You sure are... You both are."

An idea popped into Jade's head. She crawled under her sister and engulfed her  
little cock.

"Sis?! Oh my god, that feel amazing. Aaron in my ass and you on my uh..."

"Your clit," said Aaron.

"M-my clit..."

"I mean, it's small enough to be one."

"That doesn't make me feel better."

"Your girl-dick?"

"I like that better."

"Keep sucking my girl-dick sis."

Soon Jamie was cumming, filling his sister's mouth with the small amount of  
semen he was able to produce. Jade swallowed his load and crawled out from  
under him. Jamie collapsed onto the bed letting Aaron fuck him prone.

"How was your first blowjob sis?"

"Incredible."

"Those girls should have given you a chance. That was the easiest BJ I've ever  
given."

"Does that mean you wouldn't mind doing it again?"

"Not if you don't mind returning the favor."

"Not at all. Bring that pussy over here."

"Now? I'm full of cum."

"It's not like I haven't drank his cum before."

"Oh. Yeah I guess that's true."

Jade got up and sat in front of her sister who went to work right away.

"I'm getting close," said Aaron.

"She's a little preoccupied," said Jade, "but I'm 90% sure she'd tell you to  
blow in her ass."

And Aaron did just that, once again filling his best friend's ass with his hot  
cum. Jamie continued to eat Jade until she came and the three laid together.  
Jamie was now an cum filled mess having taken two loads in the ass and drinking  
a third out her sister's pussy. They were all tired, but Jade brought them back  
to reality.

"We have to get up."

"I'm not ready yet," said Jamie.

"Mom's going to be home in like 20 minutes. Sooner if they let her go early."

"Fuck, is it that late?" said Aaron.

"Yep, time flies when your fucking. We have to clean up this mess. This room  
smells and looks like a brothel."

"Shit what do we do," said Jamie. Jade took charge:

"You're a mess. Go get a shower, clean all the cum off of you... and out of  
you. Make sure to get your makeup off too. Come out of the shower in boy  
mode, because mom might already be here at that point. Aaron, go clean  
yourself up and get dressed then come back and help me clean the room."

They went to work according to Jade's plan and were quickly able to restore  
order. When their mom came home, there wasn't a drop of cum in sight.

\--------------------

Epilogue:

Aaron and the sisters remained in a polyamorous relationship for the rest of  
their lives, though legally Aaron was married to Jamie.

Jamie did eventually come out to his mom, who tried her best to be supportive  
despite not quite understanding where Jamie was coming from or how he could want  
to be a woman so suddenly.

Years later Jamie would find out through a genetic test that she was always  
meant to be a girl. She and Jade had actually been identical twins, or rather  
they were supposed to be, but Jamie was born with a small mutation that  
effected her development. This is why she had an abnormally small penis and  
why she had been so effeminate as a boy.


End file.
